Cameron Diaz’s Best Red Carpet Looks Ever: All the Times She Won Best Dressed

Don’t call it a comeback, but Cameron Diaz has officially returned to the red carpet, making her first appearance on the crimson rug on Wednesday, January 15, after taking a ten-year hiatus from Hollywood.

When she stepped out for the Berlin premiere of her new Netflix film Back in Action, she turned heads in a full Gucci look with a decidedly laid back twist that was right in line with her eternally cool California girl aesthetic. She ditched high heels in favor of Gucci penny loafers that grounded dark denim mom jeans and a sheer blouse, then threw an oversize coat on top for an extra layer of swagger.

But former model Diaz, 51, has always been a red carpet standout, and her celebrity peers have long praised her directional style, a unique brand of poetic bohemia that consistently sets her apart.

In her Vogue May 2003 cover story, Diaz’s Charlie’s Angels costar Lucy Liu said of her friend’s wardrobe: “For Cameron, it’s an art form, and it’s all about transformation and change — like turning a skirt into a tube top. Something could cost $10 or $10,000 — either way, if she’s comfortable in it. She makes it work. She defines her own fashion, and people follow it.”

During her mercurial rise in Hollywood, her red carpet aesthetic read like a masterclass in ’90s-era minimalism. She was a fan of all-black little black dresses that highlighted her mile-long legs and she’d add a kicky red heel to simple black pants with a halter top and a cardigan draped over her shoulders. She loved a jaunty hat, a midriff-baring crop top and lots (and lots) of blue eyeshadow — looks that would feel right at home on Gen-Z style stars of today.

As she landed bigger roles, she occasionally landed on the worst-dressed list. At the 2002 Academy Awards she wore an Emanuel Ungaro Haute Couture kimono dress that is now considered ahead of its time.

“Cameron was a collaborator. She was always open to mixing designers. She looked beautiful in clothes and she was a pleasure. Cameron was ahead of everyone,” her then-stylists, Clare and Nina Hallworth, have said. “She wore what felt right.”

More than 20 years later, a rewind of some of her best looks stand to serve as definitive proof that Diaz was always a red-carpet winner. Below, take a look back at 17 of our favorite Diaz moments, from the 1997 My Best Friend’s Wedding New York City movie premiere to 2007’s “Poiret: King of Fashion” Costume Institute Benefit at The Metropolitan Museum of Art.